Ethanol → 1,2-Diethyl-4-pyrazolidinamine

HRID 1105693Notes

Reaction equation

HRID 1105693 reaction equation
[N+:1]([CH:4]1[CH2:8][N:7]([CH2:9][CH3:10])[N:6]([CH2:11][CH3:12])[CH2:5]1)([O-])=O.C(O)C>C1(C)C=CC=CC=1.[Ni]>[NH2:1][CH:4]1[CH2:8][N:7]([CH2:9][CH3:10])[N:6]([CH2:11][CH3:12])[CH2:5]1

Participants

5

Reactant 2

HCID 702EthanolHCID 104421804-Nitro-1,2-diethyl-pyrazolidine

Product 1

HCID 5591991,2-Diethyl-4-pyrazolidinamineYield 85.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 1140TolueneSolvent

Procedure

To a solution of approximately 3.0 g (0.016 mole) of 4-nitro-1,2-diethyl-pyrazolidine in 100 ml of toluene was added 60 ml of anhydrous ethanol and 2 g Raney nickel (washed three times with anhydrous ethanol). The mixture was added and hydrogenated for three hours at about 30 psi. The mixture was filtered to give a light yellow solution. The solvents were evaporated at reduced pressure giving the colorless liquid, 1.95 g of the title product, b.p. 113°-115° C./40 mm. The dimaleate salt melted at 119°-120° C.

Workup

  1. additionThe mixture was added
  2. filtrationThe mixture was filtered
  3. customto give a light yellow solution
  4. customThe solvents were evaporated at reduced pressure

Sources & evidence

ORD record
ord-911f1777f1a74196ab32e56526dcf604
Source dataset
uspto-grants-1982_01
Patent number
US04309552

Reaction notes

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